1,2,3,4-Tetrahydroisoquinoline → N-[3-(1,2,3,4-Tetrahydroisoquinolin-2-yl)propyl]acetoacetamide

HRID 964231Notes

Reaction equation

HRID 964231 reaction equation
Br[CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:11])[CH2:7][C:8]([CH3:10])=[O:9].[CH2:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14][NH:13]1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14][N:13]1[CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:11])[CH2:7][C:8]([CH3:10])=[O:9]

Participants

5

Reactant 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 11430Potassium CarbonateHCID 23004079N-(3-bromopropyl)acetoacetamide

Product 1

HCID 23004192N-[3-(1,2,3,4-Tetrahydroisoquinolin-2-yl)propyl]acetoacetamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of N-(3-bromopropyl)acetoacetamide (4.50 g, 20.3 mmol, 1.00 equiv), 1,2,3,4-tetrahydroisoquinoline (3.30 mL, 26.3 mmol, 1.30 equiv), K2CO3 (3.64 g, 26.3 mmol, 1.30 equiv), and KI (330 mg, 1.99 mmol, 0.10 equiv) in acetone (60 mL) was stirred at reflux for 14 hours. The mixture was cooled to room temperature, filtered, and concentrated. The residue was purified by flash chromatography (SiO2, MeOH--EtOAc 0:1 to 1:9) to give 1.78 g (43%) of light yellow oil, which was characterized spectroscopically. N-(3-Bromopropyl)acetoacetamide (1.20 g) was also recovered.

Workup

  1. temperatureat reflux for 14 hours
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography (SiO2, MeOH--EtOAc 0:1 to 1:9)
  5. customto give 1.78 g (43%) of light yellow oil, which
  6. customN-(3-Bromopropyl)acetoacetamide (1.20 g) was also recovered

Sources & evidence

ORD record
ord-c5cdb0df87204c8f929ed0827d701130
Source dataset
uspto-grants-1998_06
Patent number
US05767131

Reaction notes

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